Ministrator



Patented Mar. 4, 1924.

our snares t an 7 MARTIN FREUND, DECEASED, LATE OF FRANKFORT-ON-THE-MAIN, AND EDMUND SPE'YER, OF FRANKFORT-ON-THE-MAIN, GERMANY; BY WALTER FEE-UNI), AD-' MINISTRATOR.

PRODUCT OF REDUCTION OF OXYCODEINON AND PROCESS FOR PREPARING T S 1'60 Drawing. Original application filed July 15, 1921, Serial No. 485,130. Divided and this application filed September 11, 1922. Serial No. 587,621.

(GRANTED UNDER THE PE OVISIONS 01? T ACT OF MARCH 3, 1921, 41 STATE. L, 1813.)

To all whom it may concern:

Be it known that MARTIN FREUND, deceased, formerly a resident of Frankfort-onthe-Main, for whom the undersigned e WALTER FREUND, residing at Frankfort-ont-he-Main, citizen of the German Republic, is acting administrator, and I, EDMUND SPEYER, a resident of Frankfort-on-the- Main, a citizen of the German Republic, 10 have invented certain new and useful Improvements in a Product of Reduction of Oxycodeinon and Processes for Preparing the Same, (for which we have filed applications in Germany, April 14:, 1916; Austria, 15 Dec. 9, 1916; Hungary, Dec. 9, 1016; Switzerland, Dec. 7,1916; Spain, Aug. 18, 1920; Czechoslovak Republic, Feb. 10, 1920; Norway Netherlands, Dec. 31, 1919; Denmark, Dec. 29, 1919; and Sweden, Jan. 20, 1920), of which the following is a clear, ,full, and exact description. 7 p

The subject of this'inyention is dihydrooxycodeinon, an unknown derivative of oxycodeino na product described in the German Letters Patent No. 286,431and the process of preparing the same.

Oxycodeinon, having the formula (3 E NO and a melting point of 273 C., by boiling with a colloidal solution of palladium chloride, is reduced to dihydrooxycodeinon of the -formula C H NO' Dihydrooxycodeinon prepared in such manner is actually identical with dihydrooxycodeinon as prepared in accordance with the specificabcr 485,130. filed July 15, 1921, from which this application is a divisional application.

The identity is shown by the following 40 facts:

Dihydrooxycodeinon prepared in accordance with this application crystallizes from alcohol in long jagged columns melting at 222 C. and yields well crystallized salts.

Its hydrochloride C H NO .HCI crystallizes from water or diluted alcohol in col- Dec. 30, 1919; Italy, Feb. 23, 1920;

tion of the patent application Serial Numumns melting at- 268 to 270 C. Its free base is precipitated from solutions of the salts by ammonia, soda or alkalies; it is unsoluble in excess of alkalies. It combines with methyl iodide to form C I-L NG...- CH .I a compound representing prisms which decompose at 251 C. Its ketone character is shown by the formation of an oxime, the hydrochloride of which:

is isolated in small sticks decomposing at 275 to 278 C.

The new dihydrooxycodeinon is to be used in medicine and pharmacy.

. E sample.

dissolved in 10 c. c. of water and make up.

with water to a total of 200 c. 0. Keep shaking this mixture and pass a stream of hydrogen into it until no more is absorbed.

-VVhen saturation is complete filter and add ammonia to the filtrate, whereupon dihydrocodeinonewill be thrown out in correspondin amounts.

Ilaving ,thus described this invention, what we claim is:

The process of preparing dihydrooxycodeinon, melting at 222 C., which consists in reducing oxycodeinon in an acetic acid solution by molecular hydrogen in the presence of palladium chloride.

In testimony whereof we have hereunto signed our names in the presence of the two subscribing witnesses.

Dr. WALTER FREUND,

Administrator of Martin Freumi, deceased.

' Privotdozent Dr. EDMUND SPEYER.

Witnesses:

Professor Dr. Fnrrz MAYER, Dr. F. N. 

